Fantasy Fest in Key West - Schedule of Events

Key West, FL -

Here’s the schedule of events…so far. Please keep checking back for updates, we’ll do our best to keep you informed. If in doubt, email us at events@tripsmarter.com and we’ll find out what you don't know…or something like that!

This year, Key West celebrates 32 years of Fantasy Fest with even more fantastical fun shared as usual by more than 70,000 costumed partygoers from all over the world. This year's theme is "Aquatic Frolic".

Fantasy Fest 2011 promises to have it all! Parades, costume contests, street parties, and much more! Can't wait for Fantasy Fest 2011? Check out our Fantasy Fest Photo Gallery for tons of great photos from previous years!

Friday, October 21st

Goombay
Tastes, sights and sounds of the Caribbean in Bahama Village, located at Duval and Petronia steets. This family friendly street party continues Saturday! Noon to midnight; FREE.

Royal Coronation Ball
“Meet Key West’s Royal Family and vote for the King and Queen of Fantasy Fest 2011 at the “Lost City of Atlantis”; a benefit for AIDS Help; 6:00 p.m.; (305) 296-6577; Suggested donation; Southernmost Café, 1319 Duval Street.

Saturday, October 22nd

Goombay
This family friendly party continues in Bahama Village! Noon - midnight; FREE

Friends of Fort Taylor's Vampire Ball
Once again everyone is invited to join us for an evening with the undead. The best party on the darker side of paradise is taking place at the Haunting of Fort Taylor, from 8pm to 11pm. Experience this bizarre affair including music from the Ghost of Kid Kelly who will turn the floor into “Dancylvania”! There will also be food drinks and the “He or she who ‘sucks’ most in Key West” costume contest. For more info go to www.keywestvampires.com. Sponsored by the Friends of Fort Taylor, and haunting people from Ghost to Ghost, the Vampires Ball 2011 will be an evening you won’t want to ‘dismember’! Missing this party would be a Grave mistake.

The Twirling Buoy Salacious Sideshow
Key West Burlesque has fashioned a fantastical Fantasy Fest show to titillate your wettest and wildest fancies! The Salacious Sideshow is a raucous ride down into the depths of an old circus carnival full of sordid seductresses and marvelously mischievous characters. Partakein comedic and variety numbers that will beguile and tease you between daring exhibitionism and dance numbers with just the right amount of naughty. Be thrilled by the devilish dancing dragon, enthralled with the worlds smallest 1000 armed lady, and dare to look away from the lion taming man eater! The Twirling Buoy laughs in the face of convention and bares enough to boggle your mind! The gorgeous show girls and guys propel you deep into your sideshow fantasies; you will never be the same! 8 pm at the Waterfront Playhouse.

Sunday, October 23rd

The Twirling Buoy Salacious Sideshow
Key West Burlesque has fashioned a fantastical Fantasy Fest show to titillate your wettest and wildest fancies! The Salacious Sideshow is a raucous ride down into the depths of an old circus carnival full of sordid seductresses and marvelously mischievous characters. Partakein comedic and variety numbers that will beguile and tease you between daring exhibitionism and dance numbers with just the right amount of naughty. Be thrilled by the devilish dancing dragon, enthralled with the worlds smallest 1000 armed lady, and dare to look away from the lion taming man eater! The Twirling Buoy laughs in the face of convention and bares enough to boggle your mind! The gorgeous show girls and guys propel you deep into your sideshow fantasies; you will never be the same! 8 pm at the Waterfront Playhouse.

The Wet and Wild Blue Party at Sheraton Suites
The Inaugural “Blue Party” benefiting Aids Help will be held at the Sheraton Suites in Key West on Sunday, October 23, 2011. The event will begin at 3:00 p.m. and continue through 6:00 p.m. Live entertainment will be provided by Key West favorite, Howard Livingston. Free food and refreshments, cash bar highlighted by Blue Margaritas. NFL football on TV, raffle prizes and giveaways. Tickets are just $10.00 and include a $5 complimentary raffle ticket. Tickets for the Inaugural Blue Party may be purchased in advance at 305-292-4360

Monday, October 24th

The Twirling Buoy Salacious Sideshow
Key West Burlesque has fashioned a fantastical Fantasy Fest show to titillate your wettest and wildest fancies! The Salacious Sideshow is a raucous ride down into the depths of an old circus carnival full of sordid seductresses and marvelously mischievous characters. Partakein comedic and variety numbers that will beguile and tease you between daring exhibitionism and dance numbers with just the right amount of naughty. Be thrilled by the devilish dancing dragon, enthralled with the worlds smallest 1000 armed lady, and dare to look away from the lion taming man eater! The Twirling Buoy laughs in the face of convention and bares enough to boggle your mind! The gorgeous show girls and guys propel you deep into your sideshow fantasies; you will never be the same! 8 pm at the Waterfront Playhouse.

Pinking of You!
Want to partake in a wildly fun event where you can mingle with local celebrities and bid on one-of-a-kind bra inspired creations? The Fifth Annual “Pinking of You” Decorated Bra Auction promises to be a great time for a great cause. Local artists transform bras into works of art, which are then modeled during a live auction to the highest bidder. You never know what you might see! All money raised will be donated to WomanKind, inc. to provide breast cancer education and early detection through clinical breast exams.; 6:00 p.m.; The Westin Resort Key West Resort and Marina; 245 Front St. (Special thanks to the Bolanowski’s)

Tuesday, October 25th

Capt. Tony's Party in Plaid
Experience a party that caters to all exotic lifestyles and fantasies. Weather you wear your naughty or nice plaid to attract old friends or to stimulate the new, this party is for you. Everyone is invited to a party for the ages that only the legendary Capt Tony's can host. Great music and drinks, plaid costumes, exotic people. 428 Greene St, 8 PM Free

Reddy Ice Fantasy Facade Competition
Festively decorated homes and businesses compete for cold cash! Free to enter or for more information, call the Fantasy Fest office 305-296-1817

Free Official Fantasy Fest Poster Signing Party
Meet-n-greet the award-winning artists of this year’s poster. Get up close and personal while having a lively libation or two; Crowne Plaza La Concha Hotel; 430 Duval St.; 5:00 p.m.; posters for sale.

29th Annual Headdress Ball
Don't miss this “over the top” Headdress Contest that includes an extravagant show that includes lots of Key West razzle dazzle! You never know what's going to happen next at the Headdress Ball. Cash Prizes for Best Headdress. Adult Themed. Held Rain or Shine. Doors open at 7pm. Curtain at 8pm. For more information, go to www.headdressballkeywest.com. Southernmost Hotel on the Beach, 508 South Street. This event sells out, so please purchase tickets early.

Finnegan's Wake Green Party
Come celebrate the ultimate Irish party! Party starts at 7pm til the wee hours of the morning. Live Irish Music from Revels Glen. No cover if you wear green. Costume contest for 'Best Eco Green Wear'. Sign up for the Edamame Eating Contest; 320 Grinnell St.; 305-293-0222

Wednesday, October 26th

Lazy Geck Redneck Party
Hey ya'll, come on down to the Lazy Gecko Redneck Party! Gussy up in your best camo or slide into your sexiest Daisy Dukes!! Prizes for the best Redneck, Redneck Babe, Redneck couple, and Team Redneck (yeah, that's you and your best bubbas!). Party starts at 7 PM Lazy Gecko 200 Duval St

Celebrity Look-a-Like Contest
Do people always tell you that you remind them of someone famous? Well, then this is your event! Imitators of the famous and fabled vie for cash and prizes; Crowne Plaza La Concha Hotel; 430 Duval St.; Contestant sign up 8:00 p.m.; FREE to watch; FREE to enter.

Fogarty's Red Party
Fogarty’s 10th Annual Red Party! Don’t miss this often imitated, but never duplicated party with a costume contest and door prizes! Live Band. 227 Duval St.; (305) 294-7525; 9:00 p.m.; $10 per person.

Dungeon of Dark Secrets and Fetishes
Embrace your darkest desires… come one and come all (boys & girls, boys & boys, girls & girls) to play in our dungeon of fetishes! Play, voyeur, or take part in the show to unleash your darkest desires. Attire: PVC, leather, latex, uniform, period, levi, underwear, vintage, glam, cyber, burlesque, masks, wear as much or as little as you want, but dress to THRILL! 801 Bourbon Bar/Saloon 1, 801 Duval; (305) 293-9800; 9:00 p.m.

Pet Masquerade & Parade
A magical carousel of frisky pets and playful owners delightfully disguised and ready to frolic for fame and fortune; Registration for competition is at 4:30 pm; Show starts at 5:30pm; FREE to watch; $25 to enter; benefits Lower Keys Friends of Animals; Casa Marina Resort; 1500 Reynolds St. For more information call 305-304-1026

Mad Hatter Party
It’s going to be an outlandish, whimsical evening at Pete’s Dueling Piano Bar. Join us for our first ever Mad Hatter spectacle! Unleash your creativity and create a one of a kind head piece, whether it’s wickedly sexy or magically fun you are sure to have fantastic time. Cash prizes for the Best Mad Hatter! 218 Duval Street; (305) 292-7770

Thursday, October 27th

Cowboy Bill's 4th Annual Git-R-Wet T-shirt Contest
Catch the hottest ladies competing for $1500 in cash prizes in this over the top competition. Contestants model the finest and most creative cotton wet t-shirts. Drink Specials all night. VIP seating available or watch the action live from our big screens! 610 1/2 Duval street; 10 pm; (305)295-8219

Monster's Ball
Sea serpents, mermaids and other bizarre creatures of the deep! What lurks below and who’s dancing on the reef? Dive into this annual costume party and explore some surreal fantasies and some -too-real fantasies that should perhaps remain submerged! Green Parrot Bar; 601 Whitehead St.; (305) 294-6133

Pretenders in Paradise
The legendary costume competition with $10,000 in cash and prizes! Combining extraordinary creative genius and performing energy; Pier House Resort & Caribbean Spa, beachside. More details coming soon!

Sloppy Joe's 28th Annual Toga Party
“Still The Best Ancient Roman Party in Town!” To enter the contest, contestants must be dressed in toga and are encouraged to use Fantasy Fest’s theme “Aquatic Afrolic” for inspiration. Three divisions: Groups/Couples - $500 first place prize; Men’s - $250 first place prize; and Women’s - $250 first place prize. Free to enter contest; registration at 8:00 p.m. and contest begins at 9:30 p.m.; 201 Duval St. Door charge.

Dante's 5th Annual Halos & Horns Pool Party and Wet T-shirt Contest
Whether you wear the halo of an ANGEL or prefer devilish HORNS, GET WET & WILD at Dante’s for a chance to win BIG $$$! Free body painting, Live Music, Great Giveaways, Fantastic food and drink specials & our one of a kind stage in the CENTER of the POOL! The party starts at NOON & goes till 6:00, pole dancing starts at 4:30; Dante’s Restaurant & Raw Bar; 951 Caroline St, next to the ferry terminal; VIP seating is available.

Pajama and Lingerie Party
The hottest Playboy model in the world Kristy Morgan from the reality TV show "Tila Tequila" encourages you to dress sexy for this skimpy affair. Enter the $700 Hugh Hefner and Marilyn Monroe look-a-like contest, plus enjoy guest D.J.'s live. This event is guaranteed to sell out! Purchase advance VIP tickets online at www.keystix.com; Mangoes 700 Duval St; (305) 304-1188.

Friday, October 28th

Pimp and Ho Party
America's #1 movie star, Ron Jeremy, invites you to come fulfill your fantasy at this exotic dance party. Enter the $700 Mr. Pimp and Ms. Ho costume contest, plus enjoy guest D.J.'s live. This event is guaranteed to sell out..

11th Annual Living Art Airbrush Expo
Contestants will use the human form as a living canvas for artistic expression in competition for $2000 in cash; drink specials and live entertainment! Painting and partying start at 6:00 p.m., judging begins at 9:00 p.m. Sunset Pier at Ocean Key Resort; (305) 295-7045; FREE.

Maquerade March
Join the crowd as they parade through Old Town with music and noisemakers! Thirst quenchers provided at selected guesthouses. Begins at the Key West Cemetery Frances Street entrance but revelers can join the mad march anywhere along the two routes! Start marching at 5:00 p.m.; All welcome; FREE.

Rum Barrel's 5th Annual Pirate Bash
Dress and drink like a pirate at the Rum Barrel’s most outrageous pirate bash in the world! More than $1500 in cash prizes for the best pirate and wench costumes, great music on the rooftop stage, and awesome rume rum specials. For more info call (305) 292-7862.

Fantasy Fest Street Fair
Duval Street’s mille-long eater-tainment extravaganza features arts and crafts, food vendors, lively libations and costumed frivolity; Noon to 10:00 p.m.

801 Bourbon Bar Tea Dance
Plenty of sugar and spice at this “tea in the street” party; Live D.J., cool drinks, dancers, drag queens and celebrities; (305) 294-4737; 801 Duval St.; 1:00 p.m.; FREE.

Fetish & Fantasy Party at the Island House for Men
Envision yourself in a maze of mystery and excitement. Pursue your fantasies at the only all male event held during Fantasy Fest. This clothing optional event for adult men is co-sponsored by the Key West Wreckers. Come feel the thrill. Doors open at 9:00 pm. Clothes check provided. Purchase advance VIP tickets online at www.keystix.com. 1129 Fleming St - 305-294-6284.

Saturday, October 29th

Captain Morgan Fantasy Fest Parade
Join 70,000 frolicking partygoers as this year’s parade surfs down Duval Street. Featuring glittering floats, marching bands and dancing groups, it doesn’t get any wilder than this! Parade steps off at 7:00 p.m.

Epidermal Arts and Torso Tapestries
Art lovers gather for this bona fide cultural event to determine the best-illustrated bodies. The battle of the emblazoned bods elevates this art form to something aesthetic, creative and maybe even poetic; Green Parrot Bar at 601 Whitehead St.; (305) 294-6133.

Duval Street Promenade
Sassy entertainers, enticing food and spirited libations tempt costumed merrymakers as they party from the Gulf to the Atlantic; Noon to 10:30 p.m.; FREE.

Sunday, October 30th

The Fat Lady Sings Tea Dance
As the saying goes, “It ain’t over ‘til the fat lady sings.” Everyone will be at La Te Da from 4:00 p.m. to 9:00 p.m. for the last official event of Fantasy Fest 2011. D.J. Junior provides the music for the very last hoorah. La Te Da Hotel, Restaurant, Cabaret and Bars at 1125 Duval St.; (305) 296-6706; $5

Children's Day
A family event featuring food, games, arts and crafts and a costume contest for children. Bayview Park at Truman Ave. and Eisenhower Dr.; Noon - 5 p.m.; 305-292-8912